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Our top choices for Winchester hotels

Fairfield Inn & Suites Wilmington New Castle

Fairfield Inn & Suites Wilmington New Castle
3.0 star property
New Castle
8.8 out of 10, Excellent, (994 reviews)
"Nice, clean, staff is great!"
United States
Arthur
The price is CA $150
CA $167 total
includes taxes & fees
Apr 26 - Apr 27
Fairfield Inn & Suites Wilmington New Castle

Holiday Inn Express & Suites Wilmington-Newark by IHG

Holiday Inn Express & Suites Wilmington-Newark by IHG
2.5 star property
Newark
9.4 out of 10, Exceptional, (1,003 reviews)
"Friendly staff, clean room comfortable beds and pillows. "
United States
KANDRA
The price is CA $160
CA $177 total
includes taxes & fees
Apr 26 - Apr 27
Holiday Inn Express & Suites Wilmington-Newark by IHG

Comfort Inn & Suites Newark - Wilmington

Comfort Inn & Suites Newark - Wilmington
2.5 star property
Newark
9.0 out of 10, Wonderful, (1,092 reviews)
"Great clean hotel and friendly staff"
United States
Michael
The price is CA $128
CA $142 total
includes taxes & fees
May 11 - May 12
Comfort Inn & Suites Newark - Wilmington

Baymont by Wyndham Newark at University of Delaware

Baymont by Wyndham Newark at University of Delaware
2.5 star property
Newark
8.0 out of 10, Very good, (1,007 reviews)
"The rooms are very clean, the beds are very very comfortable and the staff is great. Other guest can be quite noisey, but all in all my stay was great."
United States
Jeanette
The price is CA $110
CA $122 total
includes taxes & fees
Apr 19 - Apr 20
Baymont by Wyndham Newark at University of Delaware

Ramada by Wyndham Newark/Wilmington

Ramada by Wyndham Newark/Wilmington
3.0 star property
Newark
7.2 out of 10, Good, (1,008 reviews)
"Yes breakfast was awesome room comfortable cozy "
United States
Beverly
The price is CA $102
CA $113 total
includes taxes & fees
Apr 19 - Apr 20
Ramada by Wyndham Newark/Wilmington

Embassy Suites by Hilton Newark Wilmington South

Embassy Suites by Hilton Newark Wilmington South
3.5 star property
Newark
8.2 out of 10, Very good, (1,001 reviews)
"Pleasant stay, clean and convient. "
United States
Molly
The price is CA $157
CA $174 total
includes taxes & fees
Apr 26 - Apr 27
Embassy Suites by Hilton Newark Wilmington South

Courtyard by Marriott Newark-University of Delaware

Courtyard by Marriott Newark-University of Delaware
3.0 star property
Newark
9.0 out of 10, Wonderful, (557 reviews)
"Our stay was very pleasant. "
United States
Karen
The price is CA $168
CA $187 total
includes taxes & fees
Apr 19 - Apr 20
Courtyard by Marriott Newark-University of Delaware

Courtyard By Marriott New Castle

Courtyard By Marriott New Castle
3.0 star property
New Castle
8.6 out of 10, Excellent, (263 reviews)
"Bar and food was great! Efficient and friendly staff at reception. "
United States
Pamela
The price is CA $180
CA $200 total
includes taxes & fees
Apr 17 - Apr 18
Courtyard By Marriott New Castle

Deluxe Inn Elkton

Deluxe Inn Elkton
Elkton
10.0 out of 10, Exceptional, (1 review)
"The room was nice and clean."
United States
steve
The price is CA $95
CA $107 total
includes taxes & fees
May 16 - May 17
Deluxe Inn Elkton

Best Western Plus Newark/Christiana Inn

Best Western Plus Newark/Christiana Inn
2.5 star property
Bear
8.4 out of 10, Very good, (231 reviews)
"Staff was very friendly, professional, and informative. Breakfast was good. Good variety of items to choose from. We would stay there again!"
United States
chris
The price is CA $128
CA $142 total
includes taxes & fees
Apr 29 - Apr 30
Best Western Plus Newark/Christiana Inn

Fairfield Inn by Marriott Kennett Square Brandywine Valley

Fairfield Inn by Marriott Kennett Square Brandywine Valley
3.0 star property
Kennett Square
8.8 out of 10, Excellent, (1,000 reviews)
"Wonderful location and great stay. Smells amazing!"
United States
sherine
The price is CA $128
CA $142 total
includes taxes & fees
Apr 26 - Apr 27
Fairfield Inn by Marriott Kennett Square Brandywine Valley

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (675 reviews)
"Great location and nice place to stay. Walk to nearby things to do and enjoy. "
United States
Sharon
The price is CA $139
CA $154 total
includes taxes & fees
Apr 19 - Apr 20
Holiday Inn Express & Suites Middletown by IHG

Woodspring Suites Wilmington Riverfront

Woodspring Suites Wilmington Riverfront
2.5 star property
South Wilmington
8.2 out of 10, Very good, (184 reviews)
"Clean rooms just a good place to stay in downtown Wilmington 10/10"
United States
Shuaka
The price is CA $123
CA $135 total
includes taxes & fees
Apr 20 - Apr 21
Woodspring Suites Wilmington Riverfront

SpringHill Suites by Marriott Newark Downtown

SpringHill Suites by Marriott Newark Downtown
2.5 star property
Newark
9.4 out of 10, Exceptional, (826 reviews)
"Super friendly and responsive staff, very clean. Pool was not working during our stay but exercise room was great. Will stay again."
United States
Jennifer
The price is CA $189
CA $209 total
includes taxes & fees
Apr 26 - Apr 27
SpringHill Suites by Marriott Newark Downtown

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (981 reviews)
"Cleaning lady and front desk were very frindly, helpful, speedy & great at there job."
United States
Mary
The price is CA $71
CA $79 total
includes taxes & fees
Apr 22 - Apr 23
Super 8 by Wyndham Havre De Grace Aberdeen Area

Relax Inn

Relax Inn
2.0 star property
New Castle
6.6 out of 10, (17 reviews)
"clean, quiet, and low cost. Who could ask for more?"
United States
Jefferson
The price is CA $99
CA $110 total
includes taxes & fees
Apr 16 - Apr 17
Relax Inn

Wingate by Wyndham North East

Wingate by Wyndham North East
2.5 star property
North East
8.0 out of 10, Very good, (970 reviews)
"Good stay. The room was clean, bed was super comfortable and the shower was great. "
United States
DeAnda
The price is CA $128
CA $143 total
includes taxes & fees
Apr 26 - Apr 27
Wingate by Wyndham North East

Candlewood Suites Newark South - University Area by IHG

Candlewood Suites Newark South - University Area by IHG
2.5 star property
Newark
8.4 out of 10, Very good, (590 reviews)
"Staff was amazing!!!!! Hotel clean and neat!!!"
United States
Victoria
The price is CA $105
CA $116 total
includes taxes & fees
Apr 26 - Apr 27
Candlewood Suites Newark South - University Area by IHG

Four Points by Sheraton Newark Christiana Wilmington

Four Points by Sheraton Newark Christiana Wilmington
3.0 star property
Newark
8.2 out of 10, Very good, (1,000 reviews)
"great location/staff there excellent/super comfy spacious room / great breakfast offered"
United States
Richard
The price is CA $131
CA $145 total
includes taxes & fees
Apr 22 - Apr 23
Four Points by Sheraton Newark Christiana Wilmington

Comfort Inn & Suites North East

Comfort Inn & Suites North East
2.5 star property
North East
7.8 out of 10, Good, (675 reviews)
"Nice room"
United States
Corjuan
The price is CA $125
CA $140 total
includes taxes & fees
Apr 22 - Apr 23
Comfort Inn & Suites North East
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

What is the best area to stay in Winchester?
The best area to stay in Winchester is the historic Old Town, which is the heart of the city and offers a distinctive experience.

Old Town is a very walkable district centred around the Loudoun Street Pedestrian Mall, a brick-paved street closed to vehicle traffic. Here, you'll find a wide selection of independent shops, local restaurants, and historic buildings, including the Handley Regional Library and the Old Court House Civil War Museum. The area retains much of its 18th and 19th-century architecture, providing a pleasant backdrop for a stroll.

Couples often find Old Town ideal for a romantic getaway. The evening atmosphere is particularly pleasant, with many restaurants offering outdoor seating and the pedestrian mall providing a charming setting for an evening walk. You're also close to several historic sites, such as George Washington's Office Museum.

Solo travellers looking for convenience and a sense of place will also appreciate Old Town. Everything you need is within easy reach, from coffee shops for a morning pick-me-up to cultural attractions, all accessible on foot.
When is the best time to go to Winchester?
The best areas to stay in Winchester are the historic downtown district and the area around Apple Blossom Mall for convenience.

The historic downtown is ideal for those who appreciate history and being able to walk to attractions. This area is centred around the Old Town Walking Mall, a pedestrian-only zone lined with boutiques, restaurants, and historic buildings. You'll find landmarks like the Handley Regional Library and the Winchester-Frederick County Historical Society nearby. The streets are generally well-maintained and offer a pleasant strolling experience.

Couples often enjoy the downtown area for its romantic charm and access to fine dining and cultural experiences. They can easily spend an evening exploring the shops, enjoying a meal at one of the many independent restaurants, or catching a show at a local theatre.

For families or those looking for modern conveniences and easy access to shopping, the area around Apple Blossom Mall to the west of downtown is a practical choice. Here, you'll find a range of contemporary hotels with amenities like indoor pools and complimentary breakfast. This location provides straightforward access to major roads, making day trips to nearby attractions simple.

Families will appreciate the convenience of having shopping and casual dining options within a short drive.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchester.
How can I save on a Winchester hotel booking with Expedia?
Members always get our best prices. Find our best Winchester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from CA $79 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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